image

Total synthesis of Hispidospermidine:
Reference: Frontier, A. J.; Raghavan, S.; Danishevsky, S. J. J. Am. Chem. Soc. 2000, 122, 6151. DOI
Keywords: Li/H -> Li-Dithiane • Si-Alkynyl -> H-Alkynyl • Alkyl-OH -> Ketone-1,2-di • Ketone -> Alkyl-OH • CompRed-Ketone/Ketone+B-H • O-H -> O-SiEt3 • O-SiEt3 -> O-H • Ether-5 • Jones oxidation • Alkyl-OH -> Ketone • Alkyl-OH -> Ketone • Cu-Me+Enone-α-Si • Enone-α-Si+Cu-R • ConjAdd-Michael • Li-Dithiane+Alkyl-X • Mg-Alkyl+Ketone • Reductive amination, B-H • N-H -> N-Alkyl • Aldol-Na -> Enone • Ketone -> Ketone-α-OR • Enolsilane+MCPBA • Rubottom oxidation • ConjReduct Enone • ConjReduct-Silylation • Ketone-1,2-di • Si-Vinyl -> H-Vinyl • Enone -> Enolsilane • Robinson annulation, Stork • Ketone enolate+Enone • Carbomercuration Alkyne • Enolsilane+Carbonium •
Reagents: BuLi(n) • Ceric ammonium nitrate • Hydroxide, sodium • LiCuMe2 • Methyl vinyl ketone • HCl • Li°/NH3 • SiEt3-OTf • Perbenzoic acid, 3-chloro • Fluoride, Bu4N+ • DMSO, (COCl)2 • BH4-Na+ • SiEt3-OTf • MeMgI • HCl • CrO3, H2SO4 (Jones) • TsOH·Py • Alkyl-MgX • Cr2O7·2PyH (PDC) • BH3CN-Na+ • Hydroxide, potassium • LiN(SiMe3)2 • HgCl2 • SiMe3-Cl •

Syntheses Home